Hiscox Courageous Entrepreneur Interview Series

Interview Series Sponsored by Hiscox Small Business Insurance. Hiscox specializes in protecting IT/technology, marketing, consulting, health and beauty, photography and many other professional services businesses, tailoring coverage to the specific risks in your industry.

The day after graduating college, most of us are still celebrating or recovering from the night before. One day after now 27-year-old Adam Goldstein graduated from MIT, he started Hipmunk with co-founder Steve Huffman.

Travel-planning site Hipmunk now employs over 40 people and has raised over $40 million in funding since launching nearly five years ago. Adam describes the company as the “fastest and easiest way to plan travel, helping the traveler save time and money.” By focusing on the agony of a trip, visitors can view comprehensive search results that present the least and most agonizing travel options, showing time saved and time spent in transit depending on the option selected.

Pain Debate

While leading the MIT debate team his senior year, Adam was crowned the North American Debate Champion. As captain of the team, Adam was responsible for booking travel plans for the entire team. He quickly realized the challenges of searching, coordinating, and booking travel plans for a large group of people. His negative experiences paired with poor customer service and dull user interfaces presented an opportunity too good to pass up.

When building Hipmunk, the toughest customers Adam and Steve had to please were themselves. “We had to go through a bunch of different iterations until we found something we thought was both easy to use and also very useful – useful enough that neither of us would ever go back to anything else,” said Adam.

Creating an end-to-end product that’s better than anything else that existed was just one part of the needed solution. The product was coming together nicely, but you can’t have a travel service without travel to offer. Airlines and hotel chains are often hesitant to provide inventory to unestablished startups. “It was a chicken and egg problem.” With persistence and a little bit of luck, they were able to get their first supply just in time for Demo Day at Y Combinator. Shortly after Demo Day, Hipmunk received their first million in seed funding.

Adam first started to exercise his entrepreneurial side after teaching himself how to program in middle school. Instead of purchasing a chess clock to play games of chess, Adam built a computer program that would act as a chess clock. He soon realized he could sell his apps online. It might not seem like a lot of money now, but making $20 a week selling apps while still in middle school is pretty impressive.

Q: Would you still have become an entrepreneur if you had never learned how to code?

A: “I’m not sure it would’ve occurred to me that this was a reasonable career path unless I’d experienced first-hand how relatively easy it was to distribute software online.”

Hip Advice

Due to the complexity of the search function, Adam’s background in programming was an important aspect of building and growing the company from the start. Asked about how entrepreneurs can find a technical founder, Adam replied, “The best way to find a technical co-founder is to be one yourself.” He went on to explain that even having a “passing familiarity” with programming will help build the credibility and knowledge needed to get started and recruit other programmers.

Adam’s ventures have all come from an interest or pain he wanted to solve. Asked for his advice to aspiring young entrepreneurs, Adam recommends, “Make sure whatever you’re working on is something you have conviction about. Our conviction came from our personal experience with the problem we were trying to solve. Other people’s conviction comes from the fact that they’re excited about a large revenue opportunity and they know the market well. I’ve never seen an entrepreneur who’s been successful just trying out an idea with no excitement or reason for them to be deeply invested in it. There has to be some basis for why it’s being done, why it’s exciting to the entrepreneur, or it’s not worth spending time on.”

Listen to the full interview with Adam Goldstein below.

Additional Interview Highlights

– What was the biggest risk you faced when starting Hipmunk? “The risk of failure.”

– From his experience with the debate team, Adam learned “how to speak slowly and clearly in front of a group of people.”

– Importance of clearly communicating as CEO: “Early on, when I was making the adjustment from college to management, I hadn’t fully realized how employees can (interpret) take arguments. My style was just to debate this and see where we end up. When you’re managing people; if you say something like, “what about this?” it will be interpreted as “hey, Adam wants us to do this.” It makes it important to drive distinction between those things when talking to people.”

– Adam talks about writing his first book at the age of 16, and the importance of writing.

– Hip future: After recently launching partnerships with Yahoo! Travel and Yelp, Hipmunk is now working on new features and continuing to innovate on their search features and process.

You Might Also Like...

About The Author

Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016).
Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on Under30CEO.com, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others.
Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.